The Best Hiking Trails in Massachusetts

Stretching for approximately 11 miles, the Ashuwillticook Rail Trail winds its way through the charming Berkshire region, passing through the towns of Cheshire, Lanesborough, and Adams. The trail follows the path of a former railroad line, offering a flat and easily accessible route for walkers, runners, cyclists, and even rollerbladers....

Following the 25-mile route of the old New Haven Railroad Framingham & Lowell line, the Bruce Freeman Rail Trail is a scenic and historic rail trail that spans eight communities in Massachusetts: Lowell, Chelmsford, Westford, Carlisle, Acton, Concord, Sudbury, and Framingham....

Hiking the Freedom Trail in Boston is an enjoyable exploration of the city's rich history - a 2.5-mile journey that unfolds like pages from Boston's past and leads you past no fewer than 17 sites of interest....

The hike from Castle Island along the Boston Harbor Walk is scenic and enjoyable, offering a mix of natural beauty and maritime charm. Begin your stroll at Castle Island, an iconic spot with Fort Independence standing against the backdrop of the harbor....

The Back Bay Fens sits in the Fenway-Kenmore neighborhood of Boston, just next to the Fenway Victory Gardens and close to the Museum of Fine Arts. The Lost Emerald Necklace Trail loops around the park and the Muddy River, which - just to the north of Back Bay Ferns - joins the Charles River....

Snaking through a series of Boston neighborhoods, the Southwest Corridor Path is a paved trail leading through a narrow strip of greenery. Moving along the path is much more enjoyable than traveling on the nearby artery roads, so the trail is busy with hikers, bikers and runners - all seeking a quieter way of moving through the city....

Both of the parks covered in this hike are charming, and combining them on one hike is a great way of getting your nature fix close to Boston city centre. The parks are right next to Logan International Airport, so this is a great hike for the plane spotters out there....

This is a brilliant hike which squeezes a remarkable amount of variety into a relatively short distance. Park up at East Boston Memorial Park and walk south down the green corridor called the Mary Ellen Welch Greenway....

Jamaica Pond is a picturesque freshwater pond located in the Jamaica Plain neighborhood of Boston. Surrounded by lush greenery and scenic walking paths, it serves as something of a natural oasis in the heart of the city....

The Commonwealth Avenue Mall stretches for nearly two miles through the Back Bay neighborhood of Boston, creating a picturesque corridor adorned with trees, flowers, and monuments. It serves as both a scenic promenade and a tribute to notable figures and events in history....

The Cape Cod Rail Trail (CCRT) is a paved pathway that runs 25 miles one-way from South Dennis to Wellfleet, according to [CapeCodBike Guide.com](https://www.capecodbikeguide.com/railtrail.asp). The trail is renowned for its scenery and beauty as it tours the small communities and countryside found on Cape Cod....

Completed in 1930, Vermont's 273-mile Long Trail boasts the title of the oldest long-distance hiking trail in the United States. Built and maintained by the Green Mountain Club, the trail dissects Vermont north to south, connecting the Massachusetts State line to the Canadian border....

Mohawk Trail State Forest covers an impressive 6,000 acres of dense woodland, mountain ridges, and gorges. Renowned as one of the most scenic natural areas in Massachusetts, this state forest is naturally home to fantastic hiking trails! The loop and mountain climb mapped here begins from the Great Pines Camping Area by climbing a trail to a saddle on the mountain ridge....

This is the start of a lovely and unique journey through the heart of Boston city centre. Much of this section of the Boston Walking City Trail is on sidewalks, and even the sections of trail are easy and well-maintained, making it a straightforward hike overall....

Today's hike leads you through some famous landmarks and into an area which is as close to wilderness as you'll find in a city centre. Start out by walking the short distance from Roslindale Village to Arnold Arboretum, the famous outdoor botanical garden which is owned and maintained by Harvard University....

Despite passing through a developed part of Boston, the hike today somehow manages to link together a surprising amount of green space. The first task of the day is to follow the trail to the boardwalk around Ward's Pond and using this to access Olmstead Park....

The culmination of the Boston Walking City Trail, this is about as good as urban hiking gets! Picking up where you finished yesterday, follow the Charles River and then drop inland to Esplanade Park, Boston Public Garden and Boston Common....

Starting and finishing at Pleasure Bay Beach, this is an excellent out-and-back hike which leads you along Carson Beach to the John F. Kennedy Presidential Library. Carson Beach is famous for its sandy shoreline, exceptional views of Boston Harbor, and proximity to the city centre....

Constitution Beach sits in the Orient Heights neighborhood of East Boston, making it easily accessible from all parts of the city. The beach is peaceful but it's just across from Boston airport, so expect a bit of plane noise - a blessing or a pain depending on how much of an aviation enthusiast you are! The beach offers scenic views of the Boston Harbor and the surrounding area, and in addition to plane spotting you can enjoy watching boats sail by and take in the sights of the city skyline....

As one of the Boston Harbor Islands, Spectacle Island offers visitors a unique blend of natural beauty and cultural heritage. The island features rolling hills, sandy beaches, and panoramic views of the Boston skyline, making it a picturesque retreat from the city's hustle and bustle....